Aluminium lithium hydride → HCID 66761660, compound
Reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][CH3:18])=[CH:11][C:3]=1[C:4](OC(C)(C)C)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][CH3:18])=[CH:11][C:3]=1[CH2:4][OH:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl 2-chloro-5-(2-methoxyethyl)benzoate from the previous step (1 eq.) in anhydrous THF (0.26 M) was added, at 0° C., lithium aluminum hydride (1.0 M THF solution, 3 eq.). The resulting suspension was stirred at 0° C. for 1 h and then at RT for 1 h. After carefully quenching with EtOAc and H2O, sat. aq. sodium potassium tartrate was added. The resulting biphasic mixture was vigorously stirred at RT for 30 min and then extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a cloudy oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 90:10→70:30 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.